Thiosemicarbazone Explained

A thiosemicarbazone is an organosulfur compound with the formula H2NC(S)NHN=CR2. Many variations exist, including those where some or all of the NH centers are substituted by organic groups. Thiosemicarbazones are usually produced by condensation of a thiosemicarbazide with an aldehyde or ketone:

H2NC(S)NHNH2 + O=CR2 → H2NC(S)NHN=CR2 + H2OIn terms of their chemical structures, the CSN3 core atoms are coplanar.[1]

Occurrence and applications

Some thiosemicarbazones have medicinal properties, e.g. the antiviral metisazone and the antibiotic thioacetazone. Thiosemicarbazones are also widely used as ligands in coordination chemistry.[2] The affinity of thiosemicarbazones for metal ions is exploited in controlling iron overload.[3]

References

  1. 10.1107/S1600536812044066. Iodido[1-(propan-2-ylidene)thiosemicarbazide-κS]bis(triphenylphosphane-κP)copper(I). 2012. Wattanakanjana. Yupa. Pakawatchai. Chaveng. Saithong. Saowanit. Piboonphon. Prapaporn. Nimthong. Ruthairat. Acta Crystallographica Section E . 68. 11. m1417–m1418. 23284381. 3515154.
  2. 10.1016/S0010-8545(00)80276-3. Transition metal complexes of thiosemicarbazide and thiosemicarbazones. 1975. Campbell. Michel J.M.. Coordination Chemistry Reviews. 15. 2–3. 279–319.
  3. 10.1089/ars.2012.4540. Novel Chelators for Cancer Treatment: Where Are We Now?. 2013. Merlot. Angelica M.. Kalinowski. Danuta S.. Richardson. Des R.. Antioxidants & Redox Signaling. 18. 8. 973–1006. 22424293.

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